Synthesis of vinylpyrroles, vinylfurans and vinylindoles via a Brønsted acid catalyzed highly regio- and stereoselective cis-hydroarylation of ynamides

Tetrahedron

Volumn 62, Issue 16, 2006, Pages 3917-3927

  Zhang, Yanshi ^a  

^a GE GLOBAL RESEARCH   (United States)

Author keywords

Hydroarylation; Vinylation; Ynamides

Indexed keywords

AMIDE; CARBAZOLE DERIVATIVE; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG; VINYLFURAN DERIVATIVE; VINYLINDOLE DERIVATIVE; VINYLPYRROLE DERIVATIVE; YNAMIDE DERIVATIVE;

ARTICLE; ARYLATION; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; PICTET SPENGLER REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

BETULACEAE;

EID: 33645291247     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.079     Document Type: Article

References (74)

1. For recent reviews of imminium ions, see: (a) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311.
2. (b) Mayanoff, B. E.; Zhan, H.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431.
3. (c) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817 and references there in.
4. (a) Adam, J.; Ghosez, L.; Houk, K. N. Angew. Chem., Int. Ed. 1999, 38, 2728.
5. (b) Dowd, P.; Zhang, W. J. Org. Chem. 1992, 57, 7163.
6. (c) Brady, W. T.; Giang, Y. F.; Weng, L.; Dad, M. M. J. Org. Chem. 1987, 52, 2216.
7. (d) Marko, I.; Ronsmans, B.; Hesbain-Frisque, A. M.; Dumas, S.; Ghosez, L.; Ernst, B.; Greuter, H. J. Am. Chem. Soc. 1985, 107, 2192.
8. For reviews on ynamides, see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
9. (b) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379.
10. (a) Zhang, Y. Tetrahedron Lett. 2005, 46, 6483.
11. (b) Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681.
12. (c) Martinez-Esperon, M. F.; Rodriguez, D.; Castedo, L.; Saa, C. Org. Lett. 2005, 7, 2213.
13. (d) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
14. (e) Bendikov, M.; Duong, H. M.; Bolanos, E.; Wudl, F. Org. Lett. 2005, 7, 783.
15. (f) Couty, S.; Barbazanges, M.; Meyer, C.; Cossy, J. Synlett 2005, 906.
16. (g) Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509.
17. (h) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084.
18. (i) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511.
19. (j) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783.
20. (k) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377.
21. (l) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727.
22. (m) Klein, M.; König, B. Tetrahedron 2004, 60, 1087.
23. (n) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095.
24. (o) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 43, 4392.
25. (p) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67.
26. (q) Witulski, B.; Lumtscher, J.; Bergsträer, U. Synlett 2003, 708.
27. (r) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
28. For Hsung's recent applications of ynamides, see: (a) Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slafer, B. W.; Davis, A. Org. Lett. 2005, 7, 1047.
29. (b) Tracey, M. R.; Zhang,Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209.
30. (c) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353.
31. (d) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663.
32. (e) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547.
33. (f) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417.
34. (g) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.
35. For Hsung's synthesis of ynamides, see: (h) Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151.
36. (i) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz,K.C.M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
37. For an alternative synthesis of ynamides, see: (j) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011.
38. For excellent reviews, see: (a) Gribble,G.W. InKatritzky,A.R., Ress, C. W., Servien, E. F. V., Eds.; Comprehensive Heterocyclic Chemistry II; Pergamon: Oxford, 1996; Vol 2, pp 207-258.
39. (b) Sunderberg, R. J. Indoles; Academic: San Diego, 1996.
40. For recent applications of vinylindoles, see (a) Padwa, A.; Lynch, S. M.; Mejia-Oneto, J. M.; Zhang, H. J. Org. Chem. 2005, 70, 2206.
41. (b) Rosillo, M.; Dominguez, G.; Casarrubios, L.; Amador, U.; Perez-Castells, J. J. Org. Chem. 2004, 69, 2084.
42. (c) Kusurkar, R.; Goswami, S. Tetrahedron 2004, 60, 5315.
43. (d) Rawat, M.; Wulff, W. D. Org. Lett. 2004, 6, 329.
44. (e) Mori, M.; Nakanishi,M.; Kajishima, D.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 9801.
45. (f) Yang, C.; Wang, J.; Tang, X.; Jang, B. Tetrahedron: Asymmetry 2002, 13, 383.
46. (g) Laronze, M.; Sapi, J. Tetrahedron Lett. 2002, 43, 7925.
47. (h) Ishikura, M.; Hino, A.; Yaginuma, T.; Agata, I.; Katagiri, N. Tetrahedron 2000, 56, 193.
48. (i) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 7586.
49. (j) Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7196.
50. (k) Kuehne, M. E.; Muth, R. S. J. Org. Chem. 1991, 56, 2701.
51. (l) Kuehne, M. E.; Frasier, D. A.; Spitzer, T. D. J. Org. Chem. 1991, 56, 2696. For an excellent review, see: Ref. 6b.
52. For recent applications of vinylpyrroles, see: (a) Molina, P.; Fresneda, P. M.; Delgado, S.; Bleda, J. A. Tetrahedron Lett. 2002, 43, 1005.
53. (b) Molander, G. A.; Schmitt, M. H. J. Org. Chem. 2000, 65, 3767.
54. (c) Joseph, B.; Da Costa, H.; Merour, J.-Y.; Leonce, S. Tetrahedron 2000, 56, 3189.
55. (d) Campos, P. J.; Anon, E.; Malo, M. C.; Rodrigues, M. A. Tetrahedron 1999, 55, 10479.
56. (e) ten Have, R.; Savignac, P. Tetradedron 1998, 54, 1913.
57. (f) Peglow, T.; Blechert, S.; Stckhan, E. Chem. Eur. J. 1998, 4, 107.
58. For excellent reviews, see (g) Trofimov, B. A.; Sobenina, L.; Dmenev, A. P.; Mikhaleva, A. I. Chem. Rev. 2004, 104, 2481.
59. (h) Jones, R. A. Pyrroles; Wiley: New York, 1990; part 2.
60. For most recent examples, see: (a) Low, K. H.; Magomedov, N. A. Org. Lett. 2005, 7, 2003.
61. (b) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3185.
62. (c) Capito, E.; Brown, J. M.; Ricci, A. Chem. Commun. 2005, 1854.
63. For a related paper, see (d) Lu, W.; Jia, C.; Kitamura, T.; Fujiwara, Y. Org. Lett. 2000, 7, 2927.
64. Rappoport, Z. The Chemistry of Enamides in the Chemistry of Functional Groups; Wiley: New York, 1994.
65. For recent elegant applications of enamides, see: (a) Padwa, A.; Danca,M. D. Org. Lett. 2002, 4, 715.
66. (b) Fuch, J. R.; Funk, R. L. Org. Lett. 2001, 3, 3349.
67. (c) Maeng, J.-H.; Funk, R. L. Org. Lett. 2000, 2, 1125.
68. For Reviews on [4C2] cycloaddtion using dienamides, see: (a) Petrzilka, M.; Grayson, J. I. Synthesis 1981, 753.
69. (b) Campbell, A. L.; Lenz, G. R. Synthesis 1987, 421.
70. For recent examples of cycloadditions of dienamides, see: (a) Gauvry, N.; Huet, F. J. Org. Chem. 2001, 66, 583.
71. (b) von Wangelin, A. J.; Neumann, H.; Gords, D.; Spannenberg, A.; Beller, M. Org. Lett. 2001, 3, 2895.
72. (c) Ha, J. D.; Kang, C. H.; Belmore, K. A.; Cha, J. K. J. Org. Chem. 1998, 63, 3810.
73. (a) Jones, A. R.; Fresneda, P. M. Tetrahedron 1984, 40, 4837.
74. (b) Akgun, E.; Pindur, U. J. Heterocycl. Chem. 1985, 22, 585 and references there in.